As a recent high school graduate in June 1980, Cunningham happened upon an autocross, a driving contest held in a parking lot around a pylon-defined course against the clock.

Attempting to balance college classes with his desired career path wasn't working for him, and despite the disappointment of his family, he quit school to chase his dream.

In 1985, Cunningham joined the professional ranks of the sport, competing in the inaugural SCCA/Escort Endurance Championship piloting an SSA Toyota Supra for MPS Motorsports.

The following year he and the team entered the championship with an SSGT Nissan 300ZX Turbo before stepping up to the top class in a SS-category Chevrolet Corvette in 1987.

In 1988, MPS entered the SCCA Corvette Challenge, earning Cunningham eight top-10 finishes, including a podium at his home race at Road America.

[2] He became a force to be reckoned with in 1988 after switching to a Honda CRX Si and partnering with co-driver Lance Stewart for John Torok's Team GRR.

[4] In January 1987, Cunningham competed in a Honda for the first time, driving a first generation CRX Si in the PRO Ice Endurance Championship with an effort that would soon become RealTime Racing.

This successful venture continued in 1989 with a second generation CRX Si and a modified 4WD Civic Wagon in a pair of International Ice Racing Association series.

Cunningham very briefly switched to a BMW M3 and Nissan Sentra SE-R in 1991 and 1992 before rejoining World Challenge with his own team, RealTime Racing, in 1993.

He was three points shy again in 1994 when he finished runner-up in the Super Production Category, collecting two race wins in a Honda Prelude Si.

The 1997 Touring 1 season bore more fruit, as Cunningham collected four race wins en route to his second World Challenge Championship.

Cunningham reclaimed the Championship spotlight again in 2008, narrowly beating RealTime teammates Kleinubing and Kuno Wittmer (all in Acura TSXs) for the Touring Car crown.

[9] At the 2014 Detroit Auto Show it was revealed that Cunningham and RealTime Racing would campaign the Acura TLX in World Challenge's GT class.

In 1987 he switched to a Honda CRX Si and won T Class races at Watkins Glen (his first pro win) with Norris Rancourt, John Green, Scott Gaylord and Mark Wolocatiuk, and then at Road America with Lance Stewart.

1991 was a short season, but did bring a runner-up finish in the Watkins Glen 24-hour race with the Honda and co-drivers John Green, Lance Stewart and Daniel Veilleux.

Cunningham finished fourth, one point in arrears in this competitive battle, as his teammate's pole position in the rain at Watkins Glen gave him the advantage.

Cunningham was forced to miss a race or two due to his RTR World Challenge commitments, allowing Granlund to score enough points for the drivers' championship.

He and co-driver Kuno Wittmer stood on the podium twice in 2008 and Cunningham ended the season sixth in points[21] – earning him the ST Rookie of the Year title.

[24] Cunningham entered a HART Honda Accord in the 1996 North American Touring Car Championship winning four out of eight races in his debut season.